Water → 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

HRID 226986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 226986
C[Si](C)(C)N[Si](C)(C)C.[K].[CH2:11]([O:13][C:14]([C:16]1[C:25](=[O:26])[C:24]2[C:19](=[N:20][C:21]([CH3:27])=[CH:22][CH:23]=2)[NH:18][CH:17]=1)=[O:15])[CH3:12].[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35]Br)[N:30]=1.O>O1CCCC1.C(OCC)(=O)C>[CH2:11]([O:13][C:14]([C:16]1[C:25](=[O:26])[C:24]2[C:19](=[N:20][C:21]([CH3:27])=[CH:22][CH:23]=2)[N:18]([CH2:35][C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([Br:28])[N:30]=2)[CH:17]=1)=[O:15])[CH3:12]

Komponenten

7

Edukt 4

HCID 962WaterHCID 5373687Ethyl 7-methyl-4-oxo-1,8-naphthyridine-3-carboxylateHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 45051783Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, potassium salt

Produkt 1

HCID 577546221-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl esterAusbeute 14,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

25.6 mL of potassium hexamethyldisilazane (12.91 mmol, 0.5 M in tolene) was added to 2.5 g (10.76 mmol) of 7-Methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester dissolved in 22 mL of tetrahydrofuran and was stirred at room temperature for 15 minutes. 3.24 g (12.91 mmol) of 2-Bromo-6-bromomethyl-pyridine was added and stirred at room temperature for 2.5 h. Water and ethyl acetate were added and the layers separated. The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over magnesium sulfate, filtered and dried in vacuo. The crude product was purified on silica gel eluting with 50/50 ethyl acetate/hexane to yield 0.620 g of 1-(6-Bromo-pyridin-2-ylmethyl)-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester as a brown solid.

Aufarbeitung

  1. stirringstirred at room temperature for 2.5 h
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customdried in vacuo
  7. customThe crude product was purified on silica gel eluting with 50/50 ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-1a882ee0c2564a849d3d8dc8f859a0a9
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557213B2

Notizen zur Reaktion

Wird geladen…